Trifluoromethylthiolation/Selenolation and Lactonization of 2‑Alkynylbenzoate: The Application of Benzyl Trifluoromethyl Sulfoxide/Selenium Sulfoxides as SCF3/SeCF3 Reagents

Trifluoromethylthiolation/Selenolation and Lactonization of 2‑Alkynylbenzoate: The Application of Benzyl Trifluoromethyl Sulfoxide/Selenium Sulfoxides as SCF3/SeCF3 Reagents

The combined use of BnS­(O)­CF3/BnSe­(O)­CF3 with Tf2O as SCF3/SeCF3 reagents was implemented to realize an efficient synthesis of biologically interesting 4-(trifluoromethylthio/trifluoromethylseleno)­isocoumarins from 2-alkynylbenzoates. The mechanistic pathway was postulated to involve formation...

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Veröffentlicht in:Organic letters 2022-03, Vol.24 (11), p.2214-2219
Hauptverfasser: Shi, Haofeng, Wang, Xingzong, Li, Xiaoxian, Zhang, Beibei, Li, Xuemin, Zhang, Jingran, Yang, Jingyue, Du, Yunfei
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Sprache:eng
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Zusammenfassung:The combined use of BnS­(O)­CF3/BnSe­(O)­CF3 with Tf2O as SCF3/SeCF3 reagents was implemented to realize an efficient synthesis of biologically interesting 4-(trifluoromethylthio/trifluoromethylseleno)­isocoumarins from 2-alkynylbenzoates. The mechanistic pathway was postulated to involve formation of the electrophilic SCF3/SeCF3 species via interrupted Pummerer reactions followed by a concerted trifluoromethylthiolation/selenolation and lactonization process.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00563